Engineering covalent organic frameworks in the modulation of photocatalytic degradation of pollutants under visible light conditions

Venkata Laxma Reddy, 2011, A review of photocatalytic treatment for various air pollutants, Asian J. Atmos. Environ., 5, 181, 10.5572/ajae.2011.5.3.181 Turro, 1977, Energy transfer processes, Pure Appl. Chem., 49, 405, 10.1351/pac197749040405 Stephenson, 2018 Twilton, 2017, The merger of transition metal and photocatalysis, Nat. Rev. Chem., 1, 52, 10.1038/s41570-017-0052 Romero, 2016, Organic photoredox catalysis, Chem. Rev., 116, 10075, 10.1021/acs.chemrev.6b00057 Amos, 2020, Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis, Beilstein J. Org. Chem., 16, 1163, 10.3762/bjoc.16.103 Ameta, 2013, Photocatalytic degradation of organic pollutants: a review, Mater. Sci. Forum, 734, 247, 10.4028/www.scientific.net/MSF.734.247 Hoffmann, 2008, Photochemical reactions as key steps in organic synthesis, Chem. Rev., 108, 1052, 10.1021/cr0680336 Gisbertz, 2020, Heterogeneous photocatalysis in organic synthesis, ChemPhotoChem, 4, 456, 10.1002/cptc.202000014 Xiao, 2019, Metal–organic frameworks for photocatalysis and photothermal catalysis, Acc. Chem. Res., 52, 356, 10.1021/acs.accounts.8b00521 Wang, 2020, Covalent organic frameworks: emerging high-performance platforms for efficient photocatalytic applications, J. Mater. Chem. A., 8, 6957, 10.1039/D0TA00556H Wang, 2019, Covalent organic frameworks (COFs) for environmental applications, Coord. Chem. Rev., 400, 213046, 10.1016/j.ccr.2019.213046 López-Magano, 2020, Metal–organic frameworks (MOFs) and covalent organic frameworks (COFs) applied to photocatalytic organic transformations, Catalysts, 10, 720, 10.3390/catal10070720 Côté, 2005, Porous, crystalline, covalent organic frameworks, Science (80-. ), 310 Sharma, 2020, Recent development of covalent organic frameworks (COFs): synthesis and catalytic (organic-electro-photo) applications, Mater. Horiz., 7, 411, 10.1039/C9MH00856J Zhu, 2017, Crystallization of covalent organic frameworks for gas storage applications, Molecules, 22, 10.3390/molecules22071149 Mandal, 2017, Two-dimensional covalent organic frameworks for optoelectronics and energy storage, ChemNanoMat, 3, 373, 10.1002/cnma.201700048 Fang, 2015, 3D porous crystalline polyimide covalent organic frameworks for drug delivery, J. Am. Chem. Soc., 137, 8352, 10.1021/jacs.5b04147 Ma, 2016, Cationic covalent organic frameworks: a simple platform of anionic exchange for porosity tuning and proton conduction, J. Am. Chem. Soc., 138, 5897, 10.1021/jacs.5b13490 Ding, 2011, Construction of covalent organic framework for catalysis: Pd/COF-LZU1 in suzuki–miyaura coupling reaction, J. Am. Chem. Soc., 133, 19816, 10.1021/ja206846p Luis-Barrerra, 2019, Switching acidic and basic catalysis through supramolecular functionalization in a porous 3D covalent imine-based material, Catal. Sci. Technol., 9, 6007, 10.1039/C9CY01527B Wang, 2018, Sulfone-containing covalent organic frameworks for photocatalytic hydrogen evolution from water, Nat. Chem., 10, 1180, 10.1038/s41557-018-0141-5 Chen, 2020, Synthesis of bipyridine-based covalent organic frameworks for visible-light-driven photocatalytic water oxidation, Appl. Catal. B Environ., 262, 118271, 10.1016/j.apcatb.2019.118271 Guo, 2019, Stable covalent organic frameworks for photochemical applications, ChemPhotoChem, 3, 973, 10.1002/cptc.201900089 Kang, 2020, Rational synthesis of interpenetrated 3D covalent organic frameworks for asymmetric photocatalysis, Chem. Sci., 11, 1494, 10.1039/C9SC04882K Yuan, 2020, Sunlight-Driven synthesis of 1,2,4-thiadiazoles via oxidative construction of a nitrogen-sulfur bond catalyzed by a reusable covalent organic framework, ChemPhotoChem, 10.1002/cptc.201900263 Wang, 2020, Programming covalent organic frameworks for photocatalysis: investigation of chemical and structural variations, Matter, 2, 416, 10.1016/j.matt.2019.10.026 Xue, 2021, Visible-light degradation of azo dyes by imine-linked covalent organic frameworks, Green Energy Environ., 10.1016/j.gee.2020.09.010 Jiménez-Almarza, 2019, Imine-based covalent organic frameworks as photocatalysts for metal free oxidation processes under visible light conditions, ChemCatChem, 11, 4916, 10.1002/cctc.201901061 Ren, 2013, Low band-gap benzothiadiazole conjugated microporous polymers, Polym. Chem., 4, 5585, 10.1039/c3py00690e Kang, 2013, Tandem synthesis of photoactive benzodifuran moieties in the formation of microporous organic networks, Angew. Chem. Int. Ed., 52, 6228, 10.1002/anie.201300655 Jiang, 2013, Conjugated microporous polymers with rose bengal dye for highly efficient heterogeneous organo-photocatalysis, Macromolecules, 46, 8779, 10.1021/ma402104h Wang, 2014, A conjugated porous poly-benzobisthiadiazole network for a visible light-driven photoredox reaction, J. Mater. Chem. A., 2, 18720, 10.1039/C4TA03887H Dadashi-Silab, 2014, Microporous thioxanthone polymers as heterogeneous photoinitiators for visible light induced free radical and cationic polymerizations, Macromolecules, 47, 4607, 10.1021/ma501001m López-Magano, 2020, Incorporation of photocatalytic Pt(II) complexes into imine-based layered covalent organic frameworks (COFs) through monomer truncation strategy, Appl. Catal. B Environ., 272, 119027, 10.1016/j.apcatb.2020.119027 Wang, 2015, Molecular structural design of conjugated microporous poly(benzooxadiazole) networks for enhanced photocatalytic activity with visible light, Adv. Mater., 27, 6265, 10.1002/adma.201502735 Liras, 2016, Conjugated microporous polymers incorporating BODIPY moieties as light-emitting materials and recyclable visible-light photocatalysts, Macromolecules, 49, 1666, 10.1021/acs.macromol.5b02511 Ghasimi, 2017, A conjugated microporous polymer for palladium-free, visible light-promoted photocatalytic stille-type coupling reactions, Adv. Sci. (Weinheim, Baden-Wurttemberg, Ger., 4, 1700101 All POPs listed in the Stockholm Convention, (n.d.). http://www.pops.int/TheConvention/ThePOPs/AllPOPs/tabid/2509/Default.aspx (accessed August 25, 2021). Gill, 2004, Polybrominated diphenyl ethers: human tissue levels and toxicology, Rev. Environ. Contam. Toxicol., 183, 55 Souza, 2016, Evaluation of polybrominated diphenyl ether toxicity on HepG2 cells – hexabrominated congener (BDE-154) is less toxic than tetrabrominated congener (BDE-47), Basic Clin. Pharmacol. Toxicol., 119, 485, 10.1111/bcpt.12598 Raff, 2006, Gas-phase reactions of brominated diphenyl ethers with OH radicals, J. Phys. Chem. A., 110, 10783, 10.1021/jp0630222 Padhi, 2012, Pollution due to synthetic dyes toxicity & carcinogenicity studies and remediation, Int. J. Environ. Sci., 3, 940 Ventura-Camargo, 2015, Azo dyes: characterization and toxicity– A review, Text. Light Ind. Sci. Technol., 2, 85 Hou, 2007, The effect of substituent groups on the reductive degradation of azo dyes by zerovalent iron, J. Hazard Mater., 145, 305, 10.1016/j.jhazmat.2006.11.019 Pan, 2012, Evaluation of impact of exposure of Sudan azo dyes and their metabolites on human intestinal bacteria, Anaerobe, 18, 445, 10.1016/j.anaerobe.2012.05.002 Ma, 2015, Adsorption of methylene blue and Orange II pollutants on activated carbon prepared from banana peel, J. Porous Mater., 22, 301, 10.1007/s10934-014-9896-2 Albayati, 2016, Separation of methylene blue as pollutant of water by SBA-15 in a fixed-bed column, Arab. J. Sci. Eng., 41, 2409, 10.1007/s13369-015-1867-7 Lan, 2020, Facile fabrication of triphenylamine-based conjugated porous polymers and their application in organic degradation under visible light, New J. Chem., 44, 2986, 10.1039/C9NJ05500B Kong, 2003, Phenothiazine-based conjugated Polymers: synthesis, electrochemistry, and light-emitting properties, Macromolecules, 36, 8992, 10.1021/ma035087y Garrido-Castro, 2019, Intramolecular homolytic substitution enabled by photoredox catalysis: sulfur, phosphorus, and silicon heterocycle synthesis from aryl halides, Org. Lett., 21, 5295, 10.1021/acs.orglett.9b01911 Discekici, 2015, A highly reducing metal-free photoredox catalyst: design and application in radical dehalogenations, Chem. Commun., 51, 11705, 10.1039/C5CC04677G Ma, 2019, Visible light mediated external oxidant free selective C5 bromination of 8-aminoquinoline amides under ambient conditions, Asian J. Org. Chem., 8, 1136, 10.1002/ajoc.201900293 Park, 2012, Photocatalysis by phenothiazine dyes: visible-light-driven oxidative coupling of primary amines at ambient temperature, Org. Lett., 14, 5502, 10.1021/ol302584y Dadashi-Silab, 2017, Phenyl benzo[b]phenothiazine as a visible light photoredox catalyst for metal-free atom transfer radical polymerization, Chem. A Eur. J., 23, 5972, 10.1002/chem.201605574 Zhai, 2017, A backbone design principle for covalent organic frameworks: the impact of weakly interacting units on CO2 adsorption, Chem. Commun., 53, 4242, 10.1039/C7CC01921A Zhu, 2020, Enhancement of crystallinity of imine-linked covalent organic frameworks via aldehyde modulators, Polym. Chem., 11, 4464, 10.1039/D0PY00776E Lukose, 2011, The structure of layered covalent-organic frameworks, Chem. A Eur. J., 17, 2388, 10.1002/chem.201001290 Feng, 2019, Highly efficient photocatalytic degradation performance of CsPb(Br1–xClx)3-Au nanoheterostructures, ACS Sustain. Chem. Eng., 7, 5152, 10.1021/acssuschemeng.8b06023 Aarthi, 2007, Photocatalytic degradation of Azure and Sudan dyes using nano TiO2, J. Hazard Mater., 149, 725, 10.1016/j.jhazmat.2007.04.038 Senapati, 2011, Photocatalytic degradation of methylene blue in water using CoFe2O4–Cr2O3–SiO2 fluorescent magnetic nanocomposite, J. Mol. Catal. A Chem., 346, 111, 10.1016/j.molcata.2011.07.001 González-Muñoz, 2019, Size-selective mesoporous silica-based Pt(II) complex as efficient and reusable photocatalytic material, J. Catal., 373, 374, 10.1016/j.jcat.2019.04.015 Ogilby, 2010, Singlet oxygen: there is indeed something new under the sun, Chem. Soc. Rev., 39, 3181, 10.1039/b926014p Hayyan, 2016, Superoxide ion: generation and chemical implications, Chem. Rev., 116, 3029, 10.1021/acs.chemrev.5b00407 Samoilova, 2011, Reaction of superoxide radical with quinone molecules, J. Phys. Chem. A., 115, 11589, 10.1021/jp204891n Ouannes, 1968, Quenching of singlet oxygen by tertiary aliphatic amines. Effect of DABCO (1,4-diazabicyclo[2.2.2]octane), J. Am. Chem. Soc., 90, 6527, 10.1021/ja01025a059 Xu, 2020, Remarkably catalytic activity in reduction of 4-nitrophenol and methylene blue by Fe3O4@COF supported noble metal nanoparticles, Appl. Catal. B Environ., 260, 118142, 10.1016/j.apcatb.2019.118142 Gak, 1998, Triplet-excited dye molecules (eosine and methylene blue) quenching by H2O2 in aqueous solutions, J. Photochem. Photobiol. A Chem., 116, 57, 10.1016/S1010-6030(98)00230-5 Brasseur, 2005